I had posted this a few years ago and deleted it at one point, wanted to put it back up!
I had my first (and only) threesome about 4 years ago. The girl had been a friend with benefits for years. She was short, brunette, and worked herself into shape over the course of our time hooking up. She was my friend from high school’s roommate. We went out to a bar with a group of friends one night and she ended up back at my place. We hooked up from time to time for two years after that. She was a perfect fwb, she was down to try anything, always horny, and when we weren’t hooking up we would stay out of each others business. We had some fun times together, we both got more experienced with anal, she like being tied to the bed, and she’d wake me up in the morning by sucking my cock. For one of our most memorable encounters, she blindfolded herself, put headphones in, and laid naked on her bed with the door to the apartment unlocked. I let myself in and the moment she realized I was in her apartment was when my dick plunged into her pussy.
Eventually she started seeing a guy, things got serious, and she wanted to cut things off. Things must have been going well, they got an apartment together and she stopped texting me when she was feeling frisky. One afternoon I was feeling pretty horny, so I through out an idea that went over way better than expected.
She had always been adventurous, so I asked if she wanted to fuck both of us at once. I didn’t have any interest in guys, but I was itching to fuck her again, if I had to share her with another guy it would be worth it. She didn’t seem too excited at first, but said she would mention it to her boyfriend and let me know, so it wasn’t a flat out “no”. I didn’t hear back for awhile, and assumed that would be the end of it.
To my surprise, she got back to me about a week later asking if I wanted to come to their apartment that weekend. Of course I said I would love to, but I made it clear I was only interested in fucking her, although I would be willing to try to DP her if that was something she was interested in. She was on the same page and we setup the time to meet.
I got to their place in the evening in jeans and a t shirt. They were both wearing sweats, none of us were planning to stay dressed for long. She had put a little bit of makeup on, it wasn’t her style, but she knew I loved it when she left a wring of lipstick around my cock. He was taller than me, hairy, with a beard and a little bit of a belly. Everybody seemed to know the plan, I hugged her, awkwardly shook his hand, and we all kind of shuffled to the bedroom.
She sat on the end of the bed with one of us on each side. She gave him a quick peck, then turned to start making out with me. My hands went straight to their familiar home around her breasts, he kissed the back of her neck while rubbing her thigh and ass. Our shirts were all gone pretty quickly and she started switching between making out with both of us. While she was making out with him, I popped her breasts out of her bra and started sucking on them. To thank me for my efforts she started to unzip my jeans and started to snake my dick out of my boxers.
It turns out she had been fishing his dick out at the same time, and shortly we were both taking turns making out with her while the other sucked on a tit and she had a hand dedicated to jerking each of us off. It was at this point I got my first good look at his cock, he was smaller than me, but maybe a little fatter. She always loved sucking and fucking my cock, I began to get the feeling she was open to the threesome so that she could have it back inside her.
After a few more minutes of jerking us off, she took charge of the situation in a way I had not seen from her before. She pressed us both on our backs, yanked our pants the rest of the way off. She kneeled at the foot of the bed and started to alternate sucking each of us off. Blowjobs were never her speciality, but she couldn’t be faulted for lack of effort. She would slide her lips up and down the shaft for awhile, then take as much as she could in her throat. I think everyone involved noticed she was taking all of him in her mouth, but could only make it about 3/4 of the way down my shaft.
After about 10 minutes of enjoying her oral efforts I noticed his legs started to stiffen up and he clearly blew his load in her mouth. She dutifully swallowed, then they kissed deeply (I guess he was okay with tasting his own cum). With him sidelined momentarily she turned her full attention to me, straddling me cowgirl while he watched from the other side of the bed, limp dick in hand. It felt phenomenal to be back in her warm busy, and after all the buildup she was soaked. Everyone involved was clean, and she was on the pill, so i had the pleasure of being ridden bareback, I know she was expecting a few creameries later in the evening. She rode me aggressively with her hands on the headboard while I alternated between grabbing her tits and smacking her ass, two old favorites of hers.
Clearly not wanting to leave her boyfriend on the unattended for too long, she soon hopped off and began to go down on him, clearly wiggling her ass in the air as an invitation for me to fuck her doggystyle. As she sucked his dick back to life, I entered her from behind and started to give her a proper pounding. Once he was hard again he hopped onto his knees and we assumed the classic eiffel tower position. While no high fives were exchanged, there were some shit eating grins and approving grunts as she did her best to bring us both pleasure. Soon her pussy was too much for me, and I shot my load deep inside her.
Spent for the moment, I sat on the opposite side of the bed while I let the happy couple enjoy each others company. After some making out and fondling, he started to go down on her, with my cum still leaking out of her pussy (another sign that he was more okay with it than I was expecting). After warming her up with his mouth, he quickly hopped on top and started fucking her missionary. While he was laying into her, my dick was in arms reach, and she started jerking me off as my dick started showing some signs of life again.
Once I was getting hard again, I positioned myself next to her mouth so that he could go back to pleasing us both at once again. His pace quickened, and eventually it became obvious he had dispensed his second load in her pussy. With him back out of commission, she rolled over and put her full attention on sucking my dick. Seemingly inspired by the vigorous pumping she had received, she went down on me with a zeal I had not seen from her before. My eyes were closed as I enjoyed her swirling tongue and bobbing head when her boyfriend rejoined us. He laid next to her and started to kiss her neck, eventually leading to her taking turns sucking me and kissing him.
The evening took a turn when he asked “Can I help?”. It was probably the most anybody had said all night, it had been mostly affirmative grunts and moans of pleasure. She and I immediately locked eyes to see who would answer first. I was on cloud nine, and didn’t want to spoil the mood so I managed to get out “sure, you can help, a little”. Not wanting to be the buzzkill either she affirmed what I had said, “sure, a little”.
With that, they positioned my dick between their faces, and started to kiss with my mouth between each of their dicks. It was the first time a guy had been anywhere near my dick, and not something I would have ever been interested in, but the pleasure of two sets of lips, two tongues, working their way up and down my shaft was undeniable. I knew I wasn’t going to last long, so I closed my eyes and just enjoyed waves of pleasure they were giving me.
Moments before I knew I was going to cum, I felt a sudden change and opened my eyes to find he had taken over full dick sucking duty and had most of me in his mouth. I had never even though of myself as bi, but I was so closed to cumming that it would be irresponsible to object. She was clearly a little thrown off and nervously licked at my balls as I climaxed into his mouth. Before he could swallow, he made a move to kiss her, and she excepted nervously, obviously thrown off by what just occurred. After a few awkward moments of what I have a feeling was his attempt to swap cum between them she excused herself to clean up. Sensing something was wrong he scurried after her. Not wanting to be there for any impending drama, I took that as my cue to leave and started to get dressed.
I poked my head in the bathroom, she was turning the shower on, he was just kinda standing there (I was clearly interrupting something). I said I had to go but I had a lot of fun, they both kinda mumbled in agreement, and with that I was on my way. Unfortunately I think everyone kinda panicked, had cooler heads prevailed I think we could have kept going and even made the DP that had been discussed in the lead up happen.
I didn’t hear from them after that, until we were both at her former roommate’s wedding. They avoided me like the plague and didn’t speak to me all night. When her roommate mentioned it to me I said she probably wanted to avoid introducing her boyfriend to an ex. She never would have guessed that we had not only met, but I had blown my load in his mouth after fucking his girlfriend. Things could not have been that bad between them though, they ended up getting married some time later and are still together. I haven’t had an experience with a guy since then, nor am I looking for one, but if they were looking for a round two I don’t think I could turn them down.
Source: reddit.com/r/gonewildstories/comments/10l8wlx/mmf_y_first_threesome_m33